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Preparation method for oxo-propenylmorpholine

A technology of oxypropenyl morpholine and propenyl morpholine, which is applied in the field of preparation of oxypropenyl morpholine, can solve problems such as difficulty in obtaining, long degradation cycle, and large environmental impact, and achieve reduction of material costs and reaction steps The effect of less and simple operation

Active Publication Date: 2017-07-14
GUANGDONG BOSSIN NOVEL MATERIALS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the synthetic routes of oxypropenylmorpholine at home and abroad mainly include acryloyl chloride method and acrylic acid method, but the synthetic raw materials of these methods are expensive and the sources of raw materials are difficult
Chinese patent 201510787708.0 uses acrylic acid, polymerization inhibitor, acyl chloride reagent, and morpholine as raw materials to synthesize N-acryloylmorpholine, but these raw materials are difficult to obtain and more dangerous
Chinese patent 200710098885.3 discloses a synthetic method for preparing high-purity N-acryloylmorpholine. The patent uses acrylic acid, phosphorus trichloride, morpholine, acid-binding agent and solvent as raw materials. The product acryloyl chloride is very easy to hydrolyze and volatilize, which has a great impact on the environment and is difficult to realize industrial production
Although polylactic acid can be completely degraded in the natural environment, its degradation cycle is long, and the carbon dioxide and water produced by the degradation are difficult to directly recycle and reuse, resulting in a huge waste of resources

Method used

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  • Preparation method for oxo-propenylmorpholine
  • Preparation method for oxo-propenylmorpholine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 6.0kg morpholine, 6.0kg polylactic acid resin (molecular weight 500), 500ppm 2,6-di-tert-butyl-4-methylphenol in sequence, heat to 90°C for 2 hours, then raise the temperature to 120°C, and stir thoroughly. React for 6 hours to make the reaction complete, distill under reduced pressure and collect fractions at 120°C; add an appropriate amount of acetic anhydride and sulfuric acid to the collected fractions as catalysts, and collect the products after passing through the reaction channel at 500°C to obtain the crude acryloylmorpholine; the crude product is subjected to vacuum Rectification to obtain the refined product oxypropenyl morpholine.

[0032] The reaction formula of oxypropenyl morpholine described in the present invention is as follows:

[0033]

[0034] The product obtained was a yellowish liquid. 1 H NMR (500 MHz, CDCl 3 ) δ 6.49, 6.31, 5.71, 3.67, 3.55.

Embodiment 2

[0036] Add 6.6 kg of morpholine, 5.0 kg of polylactic acid resin (molecular weight 5000), 500 ppm of 2,6-di-tert-butyl-4-methylphenol in sequence, heat to 50°C for 2 hours, then raise the temperature to 120°C, and stir thoroughly. React for 1 hour to make the reaction complete, distill under reduced pressure and collect fractions at 120°C; add an appropriate amount of acetic anhydride and sulfuric acid to the collected fractions as catalysts, and collect the product after passing through the reaction channel at 450°C to obtain the crude acryloylmorpholine; the crude product is subjected to vacuum Rectification to obtain the refined product oxypropenyl morpholine.

[0037] The product obtained was a yellowish liquid.

Embodiment 3

[0039] Add 7.2 kg of morpholine, 5.0 kg of polylactic acid resin (molecular weight: 10,000), and 500 ppm of 2,6-di-tert-butyl-4-methylphenol to the flask in sequence, heat to 120°C for 1 hour, then raise the temperature to 150°C, and stir thoroughly. React for 4 hours to make the reaction complete, distill under reduced pressure and collect fractions at 120°C; add an appropriate amount of acetic anhydride and sulfuric acid as catalysts to the collected fractions, and collect the products after passing through the reaction channel at 550°C to obtain crude acryloylmorpholine; the crude product is subjected to vacuum Rectification to obtain the refined product oxypropenyl morpholine.

[0040] The product obtained was a yellowish liquid.

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Abstract

The invention relates to a preparation method for oxo-propenylmorpholine, which includes the steps of: performing an aminolysis reaction with polylactic acid and morpholine as raw materials; and then performing an elimination reaction under the effect of a catalyst to produce the oxo-propenylmorpholine, wherein in the aminolysis reaction, reaction temperature is 50-180 DEG C, reaction time is 1-24 h and reaction pressure is 1-5 atm; the molecular weight of the polylactic acid is 500-100000; and the molar ratio of the polylactic acid to morpholine is 1:1-2. In the method, the polylactic acid and morpholine are used as raw materials, so that the method is beneficial to recovery of the polylactic acid and reduces material cost. The method is high in yield and the product is easy to purify. The method is less in reaction steps and simple in operation and is free of generation of an acidic gas, HCl, during the reactions, so that corrosion on reaction equipment is avoided.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of oxypropenylmorpholine. Background technique [0002] Oxypropenylmorpholine is an excellent reactive diluent for UV-curable resins, and it is also an excellent monomer for synthetic resins. As a non-toxic monofunctional photocurable monomer, oxypropenylmorpholine is an important part of the photocurable material formula, which can effectively reduce the viscosity of the formula and improve the adhesion, hardness and toughness. Therefore, it is of great significance to carry out the optimization and research on the synthesis process of oxypropenylmorpholine. [0003] At present, the synthesis routes of oxypropenylmorpholine at home and abroad mainly include acryloyl chloride method and acrylic acid method, but the synthetic raw materials of these methods are expensive and the sources of raw materials are difficult. Chinese patent 201510787708.0 uses acryli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/185
CPCC07D295/185
Inventor 庞来兴李志云刘杰夫秦顿迪张慧艳
Owner GUANGDONG BOSSIN NOVEL MATERIALS TECH CO LTD